Ultrafast Au(III)-Mediated Arylation of Cysteine

Evan A. Doud, James A.R. Tilden, Joseph W. Treacy, Elaine Y. Chao, Hayden R. Montgomery, Grace E. Kunkel, Eileen J. Olivares, Nima Adhami, Tyler A. Kerr, Yu Chen, Arnold L. Rheingold, Joseph A. Loo, Christopher G. Frost, K. N. Houk, Heather D. Maynard, Alexander M. Spokoyny

Research output: Contribution to journalArticlepeer-review

11 Citations (SciVal)

Abstract

Through mechanistic work and rational design, we have developed the fastest organometallic abiotic Cys bioconjugation. As a result, the developed organometallic Au(III) bioconjugation reagents enable selective labeling of Cys moieties down to picomolar concentrations and allow for the rapid construction of complex heterostructures from peptides, proteins, and oligonucleotides. This work showcases how organometallic chemistry can be interfaced with biomolecules and lead to a range of reactivities that are largely unmatched by classical organic chemistry tools.

Original languageEnglish
Pages (from-to)12365-12374
JournalJournal of the American Chemical Society
Volume146
Issue number18
Early online date24 Apr 2024
DOIs
Publication statusPublished - 8 May 2024

Funding

A.M.S. thanks NIGMS (R35GM124746). Portions of this work were supported by University of Bath and EPSRC (to C.G.F.), NSF CHE-2003946 and NSF CHE-2153972 (to K.N.H.), NSF CHE-2003946 (to H.D.M.), and Noble Family Innovation Fund administered by UCLA California Nanosystems Institute (CNSI) (to A. M. S.). J.A.L. and E.J.O. thank NIGMS for their corresponding support: R35GM145286 and T32GM145388. This work used computational and storage services associated with the Hoffman2 Shared Cluster provided by the UCLA Institute for Digital Research and Education\u2019s Research Technology Group. The authors are grateful to Dr. Martin Phillips for his assistance with the stopped-flow experiments.

FundersFunder number
California NanoSystems Institute
University of Bath
Noble Family Innovation Fund
Engineering and Physical Sciences Research Council
National Science FoundationCHE-2003946, CHE-2153972
National Science Foundation

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint

Dive into the research topics of 'Ultrafast Au(III)-Mediated Arylation of Cysteine'. Together they form a unique fingerprint.

Cite this